Isatin → 3-(5-bromo-2-hydroxyphenyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one

HRID 545786Notes

Reaction equation

C1(CC[N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[C:7]2=[O:16])CC1.N1C2C(=CC=CC=2)C(=O)C1=O.O1C2C=CC(O)=CC=2OC1.[Br:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1>>[Br:38][C:39]1[CH:40]=[CH:41][C:42]([OH:45])=[C:43]([C:8]2([OH:15])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[NH:6][C:7]2=[O:16])[CH:44]=1

Participants

Reactant 4

HCID 7054Isatin

HCID 78084-Bromophenol

HCID 68289Sesamol

HCID 655965701-(2-cyclopropylethyl)-1H-indole-2,3-dione

Product 1

HCID 120043333-(5-bromo-2-hydroxyphenyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2B, and making non-critical variations to replace 1-(2-cyclopropylethyl)-1H-indole-2,3-dione with isatin, 1,3-benzodioxol-5-ol with 4-bromophenol, the title compound was obtained (71%) as a yellowish solid: MS (ES+) m/z 319.4 (M+1), 321.4 (M+1).

Sources & evidence

ORD record: ord-0d83adc58943489b93f11d67c2f48b06
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935721B2

Reaction notes

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